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About two and a half years ago, Andrew Dice Clay reached rock bottom. "My career was in the fucking toilet," says the veteran comedian. "I wasn't earning enough to make my monthly nut, and I had a bunch of lawsuits against me I can't talk about." Desperate for cash, the notoriously foul-mouthed entertainer decided that his only option was to try his luck in Las Vegas. "I used to be a big gambler," he says. "I could win or lose $500,000 to $700,00 within hours."

Before heading to Vegas in the summer of 2010, he had an intense heart-to-heart with his two sons. "I always taught them I didn't want them drinking, doing drugs or gambling," he says. "I'm so afraid of those things. But I told them I had to win some cash."

Against all odds, Clay won over a million dollars. "I was living like it was The Hangover," he says. "I bought a Mercedes, a Challenger, a Denali and another Mercedes for my wife. I paid off some bills and started paying off the lawsuits." But he was unable to stop gambling, and by the end of the summer he lost it all. He went home as broke as he left.

Twenty years ago Clay sold out Madison Square Garden two consecutive nights, but by this point he was back to working tiny clubs. "When I got back home I didn't want to know from show business," he says. "I didn't want to know from bills. I just wanted to get some coffee at Starbucks with my son Max."

At the coffee shop he bumped into his old friend Bruce Rubenstein, a screenwriter who often worked with Mickey Rourke in the Nineties. "He had mud on his boots and clothes," Clay recalls. "He told me he was doing construction. I told him about all my problems, and the whole time he was typing on his fucking Blackberry. I was getting pissed off, but then he says to me, 'Why didn't you ever do a little walk-on on Entourage?' I said to him, 'What do you think – I wouldn't? They never called.'"

It turns out that Entourage creator Doug Ellin is a former struggling comic, and he worshipped the Diceman back in the Eighties. He's also a close friend of Rubenstein. "He arranged for me to meet Doug the very next day," says Clay. "I met him at the Soho Club in Beverly Hills. It actually felt like a scene out of Entourage. We had a nice meeting, and I left feeling pretty good."

Clay thought that his best-case scenario was a brief cameo on the HBO show, but Ellin had other plans. He made Clay a major character on the final season of the show, playing a super-paranoid version of himself. "Doug said to me, 'I'm going to put you on my show and just wait until you see what happens,'" says Clay. As soon as the show began airing, the comic found himself filling 1,500-seat theaters for the first time in years. It was the most mainstream exposure he'd had since his glory days.

The next call was one of the most shocking moments of his life: Woody Allen wanted a meeting in New York. "I just looked at him and said, "I need you to know that Andrew is in the room, not the Diceman,'" says Clay. "I know how people perceive me. If you all know is the guy onstage going, 'Honey, suck my fucking dick,' you'd think it was some sort of an animal. I just wanted him to relax, because he's a very low-key guy. He said, 'Look, we're doing this movie, and would you read a few pages for me?'"

Allen was impressed by the reading, and Clay soon found himself on a set with Alec Baldwin, Cate Blanchett, Peter Sarsgaard and Louis C.K. "I couldn't even believe I was acting with these people," Dice says. "The movie is a heavy drama. It's not about comedy. It's probably the heaviest movie he's ever done." The film, currently untitled, is due out sometime next year.

Around the time he was filming the Woody Allen movie, Clay signed a deal with Showtime to shoot his first comedy special in 17 years. "I spent months working on the material in Vegas," he says. "I got a personal trainer and went from a 42-inch waist to a 33, and I put on some muscle. I wanted the fans to see me the right way."

Age has not mellowed the Diceman. Even by modern standards, his act is still shocking. He says "fag" so often it's easy to lose count. "Gay just isn't as funny a word as faggot," he says. "As a Brooklyn tough comic, you don't use the word gay. It's like calling girls piglets. It's a funny fucking word. I just blow everything up like a cartoon. I like to paint pictures for people that are sexually funny cartoons. That's what makes people laugh. When I'm talking about Valentine's Day I say, 'You gotta be choking her good, but God forbid you cut off her oxygen supply today.'"

Andrew Dice Clay: Indestructible, which airs on Showtime on New Years Eve, is just the beginning of Clay's big plans for 2013. The Woody Allen movie should lead to even more attention than Entourage, and he's working with writer David Ritz on his memoir. There's even talk of a movie about Clay's life, and he met with James Franco in New York about possibly portraying him in the film. "He's a real Method guy," says Clay. "But he was doing me not as Dice – he was doing the real Andrew. He had the right look for it."

In the meantime, Dice is booking comedy gigs for next year. "It's been quite a resurgence," he says. "I really have a vision. I know what people want to hear about. I talk about what happens behind closed doors. Years ago I had all these problems with women picketing my show and defacing my billboard. These people didn't know that I'm a Brooklyn bozo. I'm a comic. This isn't meant to hurt anybody. If you're Bill Maher, you talk about politics. If you're Andrew Dice Clay, it's all about sex."